Step back in time and experience the timeless charm of this 1924 Craftsman bungalow, a classic example of the beloved Sears, Roebuck and Company Walton model, one of the most popular kit homes offered between 1920 and 1930. Rich in Arts & Crafts character, this distinctive village home showcases the architectural details that make this style so enduring, including an oversized covered front porch extending beyond the main footprint of the home, distinctive porch pillars, contrasting rooflines, a charming dining room bump-out with three windows, detailed window and doorway trim, oversized windows, hardwood floors and solid wood doors. The 1,286 SF main level offers a gracious layout with a welcoming living room featuring a fireplace and an elegant opening into the spacious, sun-filled formal dining room. The kitchen is modest in size and ready for the next owner to reimagine and renovate to their own taste. A door provides access to the basement, while another leads to the covered rear porch with steps down to the side yard. Three comfortable bedrooms and a full bath complete the main level. Above, the walk-up attic presents exciting possibilities for future finishing, offering an opportunity to expand the living space while preserving the home's original character. The wraparound covered front porch features interchangeable screens and plexiglass panels to maximize outdoor enjoyment year-round. The basement level offers a versatile arrangement. Currently divided into two separate spaces, both with exterior doors from the backyard. The left leads to the mechanical and storage room, the right to a fully self-contained 1-bedroom apartment with approximately 620 SF. Steps in reveal an entry area with multiple closets, full bath, kitchen with room for breakfast table, living room, bedroom and a deep walk-in closet. Outside the apartment has a dedicated patio overlooking the expansive, flat backyard. Whether you envision an owner-occupied home with the benefit of rental income, a multigenerational living arrangement, or an investment property with two potential rental units, this property offers flexibility and opportunity. Ideally situated on East Main Street, this home enjoys the convenience of pedestrian-friendly sidewalks leading directly into the heart of Pawling Village. Explore charming boutique shops, fine dining, casual eateries, cultural attractions, outdoor recreation and the seasonal farmers market, all just a stroll away. Pawling's very own Metro-North train station provides convenient rail access for commuters and weekend travelers alike. A wonderful opportunity to own a piece of early 20th-century architectural history while enjoying the convenience and charm of village living.